Hydrochloric Acid → 7,9-Difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-thia-chrysen-2-ol hydrochloride salt

HRID 1513938Notes

Reaction equation

HRID 1513938 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]2[C:3]=1[S:4][CH:5]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)=[CH:28][CH:27]=1)[C:6]1[C:15]2=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([O:21]S(C)(=O)=O)=[CH:11]2.[OH-].[K+].[Cl-:43].[NH4+].Cl.CCOCC>CO.C(Cl)Cl>[ClH:43].[F:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[C:16]2[C:3]=1[S:4][CH:5]([C:26]1[CH:27]=[CH:28][C:29]([O:32][CH2:33][CH2:34][N:35]3[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]3)=[CH:30][CH:31]=1)[C:6]1[C:15]2=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][C:10]([OH:21])=[CH:11]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 11273238Methanesulfonic acid 7,9-difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-thia-chrysen-2-yl ester

Product 1

HCID 670047327,9-Difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-thia-chrysen-2-ol hydrochloride saltYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve methanesulfonic acid 7,9-difluoro-5-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-5H-6-thia-chrysen-2-yl ester (5.2 g, 9.0 mmol) in methanol (150 mL). Add potassium hydroxide (5.0 g, 90 mmol) and stir at room temperature. After 4 hours pour into saturated aqueous ammonium chloride and extract with methylene chloride. Dry over sodium sulfate, filter and concentrate. Dissolve residue in methylene chloride (90 mL) and add 2M HCl in ether (9 mL, 18 mmol). Concentrate in vacuo to yield 4.8 g (99%) of the title compound. LCMS Rt (0.01% heptafluorobutyric acid:1.0% isopropylalcohol:water is mobile phase A and 0.01% heptafluorobutyric acid:1.0% isopropylalcohol:acetonitrile is mobile phase B; gradient method 15 to 95% B, Purity@254 nm)=3.21 min (100%); mass spectrum (ion spray): m/z=504.3 (M+H). Chiral HPLC: 87%.

Workup

  1. extractionextract with methylene chloride
  2. dry with materialDry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-340c9335acb44245b8fc500147bec5d1
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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